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On Devarim 1:1, Rashi comments that the various places listed are in fact veiled references to episodes in which the Jewish people rebelled. Thus Moshe was offering a kind of concealed rebuke. My questions are:

  1. Why is the list of transgressions out of order? The list of rebuke items is not in chronological or any other order that I can ascertain.
  2. Why are items left out? Once he's rebuking them, why not point out every time they failed?
  3. Why is he rebuking them when they didn't do it? This is not the generation that worshiped the golden calf or sent the spies or complained at the sea. Those people are dead; this is a wholly new generation to whom Moshe seems to be speaking as if they were their parents.
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Related: judaism.stackexchange.com/q/44113 – msh210 Aug 1 '14 at 4:36
    
2 and 3 sort of answer each other - these aren't the exact individuals that "did it," so recounting every single sin that they (didn't) do wouldn't be productive. Presumably, the reason Moshe recounts these specific sins is to accomplish something through the tochecha (in this case I disagree with your translation of "rebuke" for the word), and the order might relate to the specific goal he is attempting to accomplish. – Isaac Kotlicky May 18 at 14:00

Or HaHayim has a fascinating interpretation of this pasuq (link), in which he draws out hints at 9 middot that Moshe Rabbeinu was conveying to the generation.

IMHO, Or HaHayim's interpretation addresses #2 and #3; but, at face value, doesn't address #1. My own addition to his interpretation is that, perhaps, the 9 middot are in order of importance (e.g. to be an "'Ivri" is most important and to be "Sameahh BeHelqo" is least important among these suggestions).

B"N, I will expand this answer to include a translation/summary of Or HaHayim's interpretation.

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Rashi says the allusion is to various sins, and the asker, above, wonder about the order. If Orach Chayim says the allusion is to various character traits and the order makes sense that way, I don't see how that answers the question on Rashi. – msh210 Jul 27 '14 at 15:33
    
Fair point. I forgot to tie my answer to RaSh"Y. My answer, citing Orahh Hayim, does not really contradict RaSh"Y and, at the same time, dissolves questions #2 and #3 IMHO. Also, I'm assuming the question mark in your comment is commentary on my transliteration scheme. To each his own :) – Lee Jul 27 '14 at 15:56
    
The question mark was because you linked to a page that claims to include Or Hachayim but you refer to the Orach Chayim. – msh210 Jul 27 '14 at 15:58
    
That would be me being tired. Thank you! – Lee Jul 27 '14 at 15:58
    
@msh210 If the O"H is providing the rationale/reason behind the tochecha, then it would fully explain the OP's question - Moshe is attempting to convey specific points/pitfalls/failings to them through this diatribe. Not having the O"H in front of me, I can't discuss the order, which might be implemented by severity/order of implementation. – Isaac Kotlicky May 18 at 14:02

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